EP1171665A1 - Process for the production of furfural from lignosulphonate waste liquor - Google Patents
Process for the production of furfural from lignosulphonate waste liquorInfo
- Publication number
- EP1171665A1 EP1171665A1 EP00940001A EP00940001A EP1171665A1 EP 1171665 A1 EP1171665 A1 EP 1171665A1 EP 00940001 A EP00940001 A EP 00940001A EP 00940001 A EP00940001 A EP 00940001A EP 1171665 A1 EP1171665 A1 EP 1171665A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- liquor
- reactor
- furfural
- process according
- pentose
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C07D307/48—Furfural
Definitions
- This invention relates to the production of furfural from hgnosulphonate waste liquor
- the sulphite pulping process results in a waste liquor which may contain from 0 9 to 5 6 percent of pentose which makes it a candidate for the production of furfural
- the waste liquor is thickened to a solids content of 50 percent or totally dried, the liquor or solid being sold as hgnosulphonate Pentose is an undesirable constituent of this liquor
- the waste liquor from the process is saturated with calcium sulphate, so that the high temperature required for furfural production (preferably above 200 degrees Centigrade) results in the rapid and severe deposition of calcium sulphate on the heated surfaces, which renders extended continuous operation impossible
- a process for the production of furfural from hgnosulphonate waste liquor containing pentose is characterised by maintaining the liquor at boiling point by controlled decompression for a time sufficient for the pentose to be converted to furfural and to be removed in the vapour substantially without reacting with pentose, hgnosulphonate or itself
- the reactor may be a batch or continuous reactor
- a hgnosulphonate liquor is heated by steam in a reactor which is continuously depressu ⁇ sed to pressures which are sufficient to maintain boiling of the liquor, the furfural formed migrating to the vapour phase and is discharged with the condensate and recovered
- the liquor is boiled in a continuous reactor by means of an auxiliary heat source, the liquor being discharged while the furfural formed is substantially instantaneously and completely transferred into the gas phase leaving the reactor and from which it is separated
- the liquor is heated in the reactor by means of an auxiliary heat source, the liquor being discharged while the furfural formed is substantially instantaneously and completely transferred into the gas phase from which it separated
- the auxiliary heat source is preferably heated air under pressure and this may be introduced at a low level in the reactor
- the air percolates through the liquor in the reactor, and by giving up its heat it maintains the liquor in a state of boiling before leaving the reactor
- the liquor is preferably introduced into the reactor at a temperature of between 180 and 280 degrees Centigrade
- a control circuit may be provided to maintain the pressure in the head of the reactor at a value slightly below the pressure of the entering liquor In this way the resulting liberating steam causes the liquor to undergo a minor depression to a lower temperature which forces the furfural to the vapour phase, while the heated air maintains a state of boiling of the liquor throughout the entire reactor
- the furfural produced from the pentose is immediately and completely vapou ⁇ sed as it is formed, and joins the air and some vapou ⁇ sed water to form a gaseous mixture with minimum yield loss of furfural, because reactions between furfural and pentose on the one hand, and with the lignosulphonates on the other hand cannot take place because the pentose and lignosulphonates remain in solution
- the reaction of furfural with itself is prevented by the absence of hydrogen ions in the vapour phase
- heated air instead of using heated air as the auxiliary heat source, other suitable heated gases or gas mixtures (such as hot combustion gas) or hot mercury may be used , all of which are readily separated from the liquor at the end of the reaction
- the heat required by the auxiliary heat agent is relatively small, as in essence all that is required of it is to vapou ⁇ se the furfural produced
- the low heat of vapourisation of furfural, especially at high temperatures, ensures a low auxiliary heat requirement
- the yield of furfural increases with the increasing temperature in the reactor as the losses due to reactions with pentose and lignosulphonates as well as bisulphites are suppressed at higher temperatures on account of the entropy effect on all aggregation reactions
- a pump 1 feeds a hgnosulphonate waste liquor through an in-line mixer 2, where steam injection heats it to a temperature of between 180 and 280 degrees Centigrade, thus raising the pressure accordingly
- the liquor is submitted to a minor pressure reduction in the head of a thermally insulated columnar reactor 4 and then flows downwardly to leave at the bottom via a cyclone 5 which results in decompression, cooling and thickening
- Compressed air is heated electrically in a heat exchanger and this is fed via control circuit 7 into the bottom of the reactor
- the hot air percolates upwardly, giving up its heat to the liquor and thereby maintaining the liquor in a state of ebullition before leaving the head of the reactor via a control circuit 8, a condenser 9, and an atmospheric absorption column 10 equipped with a circulation pump 1 1
- the control circuit maintains the pressure in the head of the reactor at a value slightly below the pressure of the entering liquor, so that in liberating steam the liquor undergoes a minor depression to a somewhat lower temperature while the hot air introduced at the bottom ensures continuous boiling of the liquor throughout the reactor
- the furfural formed is instantaneously and completely vapourised and joins the air and vapour to form a gaseous mixture which is condensed in 9 then collected in tank 12
- Small quantities of furfural entrained by air are recovered in the absorption column and collected in tank 12
- the input rate of the liquor and the dimensions of the reactor are chosen to match a predetermined residence time of the liquor in the reactor
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paper (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19917178 | 1999-04-16 | ||
DE19917178A DE19917178A1 (en) | 1999-04-16 | 1999-04-16 | Production of furfural from sulfite waste liquor involves heating by direct injection of steam, reaction by boiling under pressure, using easily separated ancillary, and complete vaporization by cooling and depressurization |
PCT/ZA2000/000072 WO2000063488A1 (en) | 1999-04-16 | 2000-04-14 | Process for the production of furfural from lignosulphonate waste liquor |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1171665A1 true EP1171665A1 (en) | 2002-01-16 |
EP1171665B1 EP1171665B1 (en) | 2008-08-13 |
Family
ID=7904762
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP00940001A Expired - Lifetime EP1171665B1 (en) | 1999-04-16 | 2000-04-14 | Process for the production of furfural from lignosulphonate waste liquor |
Country Status (13)
Country | Link |
---|---|
US (1) | US6642396B1 (en) |
EP (1) | EP1171665B1 (en) |
AT (1) | ATE404728T1 (en) |
AU (1) | AU5499900A (en) |
BR (1) | BR0009815B1 (en) |
CA (1) | CA2370561C (en) |
DE (2) | DE19917178A1 (en) |
DK (1) | DK1171665T3 (en) |
ES (1) | ES2307516T3 (en) |
NO (1) | NO329326B1 (en) |
PT (1) | PT1171665E (en) |
WO (1) | WO2000063488A1 (en) |
ZA (1) | ZA200108552B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102228896A (en) * | 2011-04-01 | 2011-11-02 | 山东万盛环保科技发展有限公司 | Furfural slag recycling device |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8546560B2 (en) | 2008-07-16 | 2013-10-01 | Renmatix, Inc. | Solvo-thermal hydrolysis of cellulose |
US8282738B2 (en) * | 2008-07-16 | 2012-10-09 | Renmatix, Inc. | Solvo-thermal fractionation of biomass |
CN104193705B (en) | 2008-07-16 | 2017-09-01 | 瑞恩麦特克斯股份有限公司 | The method for extracting furfural and glucose from biomass using one or more supercritical fluids |
US8119823B2 (en) * | 2008-07-16 | 2012-02-21 | Renmatix, Inc. | Solvo-thermal hydrolysis of xylose |
RU2597588C2 (en) | 2010-01-19 | 2016-09-10 | Ренмэтикс, Инк. | Production of fermentable sugars and lignin from biomass using supercritical fluids |
KR101192576B1 (en) * | 2010-11-30 | 2012-10-17 | 코오롱인더스트리 주식회사 | Continuous Preparation Method for Furfural from Xylose |
US8801859B2 (en) | 2011-05-04 | 2014-08-12 | Renmatix, Inc. | Self-cleaning apparatus and method for thick slurry pressure control |
AU2012250575B2 (en) | 2011-05-04 | 2015-03-26 | Renmatix, Inc. | Lignin production from lignocellulosic biomass |
JP2014517052A (en) * | 2011-06-22 | 2014-07-17 | ビーエーエスエフ ソシエタス・ヨーロピア | Method for dehydrating a carbohydrate-containing composition |
US8759498B2 (en) | 2011-12-30 | 2014-06-24 | Renmatix, Inc. | Compositions comprising lignin |
US9174909B2 (en) | 2012-02-02 | 2015-11-03 | Wisconsin Alumni Research Foundation | Two-stage, acid-catalyzed conversion of carbohydrates into levulinic acid |
CN103193737B (en) * | 2013-03-29 | 2015-01-28 | 山东龙力生物科技股份有限公司 | Method for preparing furfural and co-producing lignin and cellulosic ethanol via plant material |
EP3186286B1 (en) | 2014-09-26 | 2024-04-10 | Renmatix Inc. | Cellulose-containing compositions and methods of making same |
EP3626711A1 (en) * | 2018-09-24 | 2020-03-25 | Arbaflame Technology AS | Process for the production of furfural |
CN116144038B (en) * | 2022-11-02 | 2024-05-07 | 华南理工大学 | Method for preparing furfural, lignin sulfonate and high degradable cellulose by integrated multi-process coupling |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1838109A (en) * | 1930-06-06 | 1931-12-29 | Brown Co | Production of furfural |
FR1129139A (en) * | 1955-07-15 | 1957-01-16 | Paper mill waste liquor treatment process | |
US2845441A (en) * | 1955-11-16 | 1958-07-29 | Brown Co | Processes for production of furfural |
AT367473B (en) | 1980-04-10 | 1982-07-12 | Kanzler Walter | METHOD FOR OBTAINING FURFUROL, FORMIC, ACETIC ACID FROM ACID HYDROLYSATES OF PLANTS |
AT376717B (en) * | 1983-05-02 | 1984-12-27 | Chemiefaser Lenzing Ag | METHOD FOR OBTAINING FURFUROL FROM ACID WATER DRAINAGE OF THE CELLULAR EQUIPMENT AND SYSTEM FOR IMPLEMENTING THE METHOD |
US4533743A (en) | 1983-12-16 | 1985-08-06 | Atlantic Richfield Company | Furfural process |
-
1999
- 1999-04-16 DE DE19917178A patent/DE19917178A1/en not_active Withdrawn
-
2000
- 2000-04-14 CA CA002370561A patent/CA2370561C/en not_active Expired - Fee Related
- 2000-04-14 PT PT00940001T patent/PT1171665E/en unknown
- 2000-04-14 ES ES00940001T patent/ES2307516T3/en not_active Expired - Lifetime
- 2000-04-14 WO PCT/ZA2000/000072 patent/WO2000063488A1/en active Search and Examination
- 2000-04-14 US US09/958,936 patent/US6642396B1/en not_active Expired - Fee Related
- 2000-04-14 BR BRPI0009815-9A patent/BR0009815B1/en not_active IP Right Cessation
- 2000-04-14 DK DK00940001T patent/DK1171665T3/en active
- 2000-04-14 DE DE60039860T patent/DE60039860D1/en not_active Expired - Lifetime
- 2000-04-14 AT AT00940001T patent/ATE404728T1/en active
- 2000-04-14 AU AU54999/00A patent/AU5499900A/en not_active Abandoned
- 2000-04-14 EP EP00940001A patent/EP1171665B1/en not_active Expired - Lifetime
-
2001
- 2001-10-16 NO NO20015031A patent/NO329326B1/en not_active IP Right Cessation
- 2001-10-18 ZA ZA200108552A patent/ZA200108552B/en unknown
Non-Patent Citations (1)
Title |
---|
See references of WO0063488A1 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102228896A (en) * | 2011-04-01 | 2011-11-02 | 山东万盛环保科技发展有限公司 | Furfural slag recycling device |
CN102228896B (en) * | 2011-04-01 | 2013-05-22 | 山东万盛环保科技发展有限公司 | Furfural slag recycling device |
Also Published As
Publication number | Publication date |
---|---|
NO329326B1 (en) | 2010-09-27 |
CA2370561A1 (en) | 2000-10-26 |
DE19917178A1 (en) | 2000-10-19 |
ZA200108552B (en) | 2002-08-22 |
WO2000063488A1 (en) | 2000-10-26 |
BR0009815B1 (en) | 2011-03-22 |
DK1171665T3 (en) | 2008-12-15 |
US6642396B1 (en) | 2003-11-04 |
CA2370561C (en) | 2009-06-16 |
ATE404728T1 (en) | 2008-08-15 |
AU5499900A (en) | 2000-11-02 |
ES2307516T3 (en) | 2008-12-01 |
NO20015031D0 (en) | 2001-10-16 |
PT1171665E (en) | 2008-10-07 |
NO20015031L (en) | 2001-12-11 |
EP1171665B1 (en) | 2008-08-13 |
DE60039860D1 (en) | 2008-09-25 |
BR0009815A (en) | 2002-01-08 |
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